Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Reactivity of the Biheterocyclic Betaine with the para-Substituted Phenacyl Bromides for the Ring Transformation Reaction

  • Yoo, Kyung-Ho (Division of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Kim, Dong-Jin (Division of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Kim, You-Seung (Division of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Park, Sang-Woo (Division of Chemistry, Korea Advanced Institute of Science and Technology)
  • Published : 1988.06.20
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Abstract

7-Dithiocarboxy-3-phenyl-5,6-dihydro imidazo[2,1-b]thiazolium-betaine (2) was prepared by treatment of 3-phenyl-5,6-dihydro imidazo[2,1-b]thiazole (1) with carbon disulfide in acetone at room temperature. On the reaction of 2 with para-substituted phenacyl bromides (4) having the electron withdrawing property by virtue of (+) resonance (R) < (-) inductive (I) or (-) resonance (R), (-) inductive (I) effect, ring transformation product p-substituted-2-[2-[7-(p-substituted benzoyl)-5-thioxo-2,3-dihydro-1H-imidazo[1,2-c] thiazol-1-yl]-2-phenylvinylthio] acetophenone (6) was obtained; however, when R is electron donating grops with (+) resonance (R) > (-) inductive (I) effect the quarternary ammonium salt 7-(p-substituted phenyl) carbonyl methyl-3-phenyl-5,6-dihydro imidazo [2,1-b] thiazolium bromide (8) is formed. The reaction of 2 with unsubstituted-phenacyl bromide (R = H), on the other hand, gives 6a and 8a to the similar ratio, respectively.

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References

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Cited by

  1. ChemInform Abstract: Reactivity of the Biheterocyclic Betaine with the para‐Substituted Phenacyl Bromides for the Ring Transformation Reaction. vol.20, pp.1, 1988, https://doi.org/10.1002/chin.198901156
  2. Synthesis of new thiazolium betaines and the ring expansion reactionvia1,4-dipolar cycloaddition vol.32, pp.5, 1988, https://doi.org/10.1002/jhet.5570320528